Title: From Olefins to Alcohols: Efficient and Regioselective Ruthenium‐Catalyzed Domino Hydroformylation/Reduction Sequence
Abstract: Angewandte Chemie International EditionVolume 52, Issue 10 p. 2949-2953 Communication From Olefins to Alcohols: Efficient and Regioselective Ruthenium-Catalyzed Domino Hydroformylation/Reduction Sequence† Dr. Ivana Fleischer, Dr. Ivana Fleischer Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113 http://www.catalysis.deSearch for more papers by this authorDr. Katrin Marie Dyballa, Dr. Katrin Marie Dyballa Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113 http://www.catalysis.de Evonik Industries AG, Paul-Baumann-Str. 1, 45772 Marl (Germany)Search for more papers by this authorDr. Reiko Jennerjahn, Dr. Reiko Jennerjahn Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113 http://www.catalysis.deSearch for more papers by this authorDr. Ralf Jackstell, Dr. Ralf Jackstell Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113 http://www.catalysis.deSearch for more papers by this authorProf. Dr. Robert Franke, Prof. Dr. Robert Franke Evonik Industries AG, Paul-Baumann-Str. 1, 45772 Marl (Germany) Lehrstuhl für Theoretische Chemie, Ruhr-Universität Bochum, 44780 Bochum (Germany)Search for more papers by this authorDr. Anke Spannenberg, Dr. Anke Spannenberg Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113 http://www.catalysis.deSearch for more papers by this authorProf. Dr. Matthias Beller, Corresponding Author Prof. Dr. Matthias Beller [email protected] Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113 http://www.catalysis.deLeibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113 http://www.catalysis.deSearch for more papers by this author Dr. Ivana Fleischer, Dr. Ivana Fleischer Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113 http://www.catalysis.deSearch for more papers by this authorDr. Katrin Marie Dyballa, Dr. Katrin Marie Dyballa Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113 http://www.catalysis.de Evonik Industries AG, Paul-Baumann-Str. 1, 45772 Marl (Germany)Search for more papers by this authorDr. Reiko Jennerjahn, Dr. Reiko Jennerjahn Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113 http://www.catalysis.deSearch for more papers by this authorDr. Ralf Jackstell, Dr. Ralf Jackstell Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113 http://www.catalysis.deSearch for more papers by this authorProf. Dr. Robert Franke, Prof. Dr. Robert Franke Evonik Industries AG, Paul-Baumann-Str. 1, 45772 Marl (Germany) Lehrstuhl für Theoretische Chemie, Ruhr-Universität Bochum, 44780 Bochum (Germany)Search for more papers by this authorDr. Anke Spannenberg, Dr. Anke Spannenberg Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113 http://www.catalysis.deSearch for more papers by this authorProf. Dr. Matthias Beller, Corresponding Author Prof. Dr. Matthias Beller [email protected] Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113 http://www.catalysis.deLeibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113 http://www.catalysis.deSearch for more papers by this author First published: 12 February 2013 https://doi.org/10.1002/anie.201207133Citations: 92 † This work has been funded by the Deutsche Forschungsgemeinschaft (Leibniz price), the Swiss National Science Foundation (SNSF, grants for I.F.), and Evonik Oxeno GmbH. We thank Dr. C. Fischer, S. Buchholz, S. Schareina, S. Smyczek, I. Stahr, A. Koch, and Dr. W. Baumann for their technical and analytical support. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Exploring the alternatives: Ruthenium imidazoyl phosphine complexes catalyze the domino hydroformylation/reduction of alkenes to alcohols in good yields and with good selectivities (see scheme). Linear aliphatic alcohols are synthesized under reaction conditions typically used in industrial hydroformylations. Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Filename Description anie_201207133_sm_miscellaneous_information.pdf267.9 KB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1For recent reviews and compendia on carbonylation reactions, see: 1aJ. Hartwig in Organotransition Metal Chemistry, University Science Books, Sausalito, 2010, pp. 745–824; 1b Modern Carbonylation Methods (Ed.: ), Wiley-VCH, Weinheim, 2008; 1c Catalytic Carbonylation Reactions (Ed.: ), Springer, Heidelberg, 2006; 1dB. Gabriele, G. Salerno, M. Costa, Synlett 2004, 2468–2483; 1e Applied Homogeneous Catalysis with Organometallic Compounds (Eds.: ), Wiley-VCH, Weinheim, 2002. 2For recent reviews on hydroformylations, see: 2aK.-D. Wiese, D. Obst in Catalytic Carbonylation Reactions (Ed.: ), Springer, Heidelberg, 2010, pp. 1–33; 2bC. P. Casey, J. Hartwig in Organotransition Metal Chemistry: From Bonding to Catalysis, Palgrave Macmillan, 2009, pp. 751–769; 2cB. Breit in Metal Catalyzed Reductive CC Bond Formation (Ed.: ), Springer, Heidelberg, 2007, pp. 139–172; 2dP. W. N. M. Van Leeuwen, C. Claver, Rhodium Catalyzed Hydroformylation, Springer, Heidelberg, 2000. 3O. Roelen, DE 849548, 1938/1952; O. Roelen, US 2327066, 1943 (Chem. Abstr. 1944, 3631). 4For selected reviews on hydroformylations selective for branched products, see: 4aJ. Klosin, C. R. Landin, Acc. Chem. Res. 2007, 40, 1251–1259; 4bM. L. Clarke, Curr. Org. Chem. 2005, 9, 701–718; 4cB. Breit, Acc. Chem. Res. 2003, 36, 264–275; 4dF. Agbossou, J.-F. Carpentier, A. Mortreux, Chem. Rev. 1995, 95, 2485–2506. 5For selected recent examples, see: 5aM. Gottardo, A. Scarso, S. Paganelli, G. Strukul, Adv. Synth. Catal. 2010, 352, 2251–2262; 5bM. Rosales, J. A. Duran, A. Gonzalez, I. Pacheco, R. A. Sanchez-Delgado, J. Mol. Catal. A 2007, 270, 250–256; 5cD. Konya, K. Q. Almeida Lenero, E. Drent, Organometallics 2006, 25, 3166–3174; 5dE. Mieczyńska, A. M. Trzeciak, J. J. Ziółkowski, I. Kownacki, B. Marciniec, J. Mol. Catal. A 2005, 237, 246–253; 5eM. A. Moreno, M. Haukka, A. Turunen, T. A. Pakkanen, J. Mol. Catal. A 2005, 240, 7–15. 6For selected examples from our research group, see: 6aI. Piras, R. Jennerjahn, R. Jackstell, A. Spannenberg, R. Franke, M. Beller, Angew. Chem. 2011, 123, 294–298; Angew. Chem. Int. Ed. 2011, 50, 280–284; 6bI. Piras, R. Jennerjahn, R. Jackstell, W. Baumann, A. Spannenberg, R. Franke, K.-D. Wiese, M. Beller, J. Organomet. Chem. 2010, 695, 479–486; 6cR. Jennerjahn, I. Piras, R. Jackstell, R. Franke, K. D. Wiese, M. Beller, Chem. Eur. J. 2009, 15, 6383–6388; 6dR. Jackstell, H. Klein, M. Beller, K.-D. Wiese, D. Röttger, Eur. J. Org. Chem. 2001, 3871–3877; 6eH. Klein, R. Jackstell, K.-D. Wiese, M. Beller, Angew. Chem. 2001, 113, 3505–3508; Angew. Chem. Int. Ed. 2001, 40, 3408–3411. 7For compendia on ruthenium-catalyzed reactions, see: 7a Ruthenium Catalysts and Fine Chemistry, (Eds.: ), Springer, Heidelberg, 2004; 7bS.-I. Murahashi, Ruthenium in Organic Synthesis, Wiley-VCH, Weinheim, 2004. 8D. Evans, J. A. Osborn, F. H. Jardine, G. Wilkinson, Nature 1965, 208, 1203–1204. 9For selected examples, see: 9aP. Frediani, M. Bianchi, A. Salvini, L. C. Carluccio, L. Rosi, J. Organomet. Chem. 1997, 547, 35–40; 9bT.-A. Mitsudo, N. Suzuki, T. Kondo, Y. Watanabe, J. Mol. Catal. A 1996, 109, 219–225; 9cM. M. Taqui Khan, S. B. Halligudi, S. H. R. Abdi, J. Mol. Catal. 1988, 48, 313–317; 9dJ. F. Knifton, J. Mol. Catal. 1988, 47, 99–116; 9eT. Hayashi, Z. H. Gu, T. Sakakura, M. Tanaka, J. Organomet. Chem. 1988, 352, 373–378; 9fG. Süss-Fink, G. F. Schmidt, J. Mol. Catal. 1987, 42, 361–366; 9gI. Ojima, K. Kato, M. Okabe, T. Fuchikami, J. Am. Chem. Soc. 1987, 109, 7714–7720. 10K. Takahashi, M. Yamashita, Y. Tanaka, K. Nozaki, Angew. Chem. 2012, 124, 4459–4463; Angew. Chem. Int. Ed. 2012, 51, 4383–4387. 11For recent reviews, see: 11aD. B. Grotjahn, Pure Appl. Chem. 2010, 82, 635–647; 11bD. B. Grotjahn, Dalton Trans. 2008, 6497–6508; for selected examples, see: 11cC. R. Larsen, D. B. Grotjahn, J. Am. Chem. Soc. 2012, 134, 10357–10360; 11dD. B. Grotjahn, C. R. Larsen, J. L. Gustafson, R. Nair, A. Sharma, J. Am. Chem. Soc. 2007, 129, 9592–9593; 11eV. Díez, G. Espino, F. A. Jalón, B. R. Manzano, M. Pérez-Manrique, J. Organomet. Chem. 2007, 692, 1482–1495; 11fD. B. Grotjahn, Y. Gong, L. Zakharov, J. A. Golen, A. L. Rheingold, J. Am. Chem. Soc. 2006, 128, 438–453; 11gD. B. Grotjahn, D. A. Lev, J. Am. Chem. Soc. 2004, 126, 12232–12233; 11hS. Harkal, F. Rataboul, A. Zapf, C. Fuhrmann, T. Riermeier, A. Monsees, M. Beller, Adv. Synth. Catal. 2004, 346, 1742–1748. 12J. Falbe, H. Bahrmann, W. Lipps, D. Mayer in Ullmann’s Encyclopedia of Industrial Chemistry, electronic release, 7th ed., Wiley-WCH, Weinheim, 2009. 13P. Kalck, M. Siani, J. Jenck, B. Peyrille, Y. Peres, J. Mol. Catal. 1991, 67, 19–27. 14 14aM.-L. Kontkanen, L. Oresmaa, M. A. Moreno, J. Jänis, E. Laurila, M. Haukka, Appl. Catal. A 2009, 365, 130–134; 14bV. K. Srivastava, P. Eilbracht, Catal. Commun. 2009, 10, 1791–1795; 14cK.-i. Tominaga, Catal. Today 2006, 115, 70–72; 14dK.-I. Tominaga, Y. Sasaki, J. Mol. Catal. A 2004, 220, 159–165; 14eM. A. Moreno, M. Haukka, T. A. Pakkanen, J. Catal. 2003, 215, 326–331; 14fS. Jääskeläinen, M. Haukka, Appl. Catal. A 2003, 247, 95–100; 14gK.-I. Tominaga, Y. Sasaki, Catal. Commun. 2000, 1, 1–3. 15For more details, see the Supporting Information. 16For ruthenium-catalyzed carbonylations in the presence of water, see: 16aJ. Jenck, P. Kalck, E. Pinelli, M. Siani, A. Thorez, J. Chem. Soc. Chem. Commun. 1988, 1428–1430; 16bH. C. Kang, C. H. Mauldin, T. Cole, W. Slegeir, K. Cann, R. Pettit, J. Am. Chem. Soc. 1977, 99, 8323–8325. 17Rhodium-catalyzed synthesis of γ-lactones from homoallylic alcohols by hydroformylation and subsequent oxidation was reported by Grünanger and Breit: C. U. Grünanger, B. Breit, Angew. Chem. 2008, 120, 7456–7459; Angew. Chem. Int. Ed. 2008, 47, 7346–7349. 18For evidence on bidentate coordination mode of ligand 2 a, see Ref. [11]. 19 19aD. Fuchs, G. Rousseau, L. Diab, U. Gellrich, B. Breit, Angew. Chem. 2012, 124, 2220–2224; Angew. Chem. Int. Ed. 2012, 51, 2178–2182; 19bO. Diebolt, C. Müller, D. Vogt, Catal. Sci. Technol. 2012, 2, 773–777; 19cK. Takahashi, M. Yamashita, T. Ichihara, K. Nakano, K. Nozaki, Angew. Chem. 2010, 122, 4590–4592; Angew. Chem. Int. Ed. 2010, 49, 4488–4490; 19dI. I. F. Boogaerts, D. F. S. White, D. J. Cole-Hamilton, Chem. Commun. 2010, 46, 2194–2196; 19eL. Diab, T. Smejkal, J. Geier, B. Breit, Angew. Chem. 2009, 121, 8166–8170; Angew. Chem. Int. Ed. 2009, 48, 8022–8026. Citing Literature Volume52, Issue10March 4, 2013Pages 2949-2953 ReferencesRelatedInformation